US9303234B2 - Hard surface cleaners based on compositions derived from natural oil metathesis - Google Patents
Hard surface cleaners based on compositions derived from natural oil metathesis Download PDFInfo
- Publication number
- US9303234B2 US9303234B2 US13/879,792 US201113879792A US9303234B2 US 9303234 B2 US9303234 B2 US 9303234B2 US 201113879792 A US201113879792 A US 201113879792A US 9303234 B2 US9303234 B2 US 9303234B2
- Authority
- US
- United States
- Prior art keywords
- amidoamine
- metathesis
- ester
- sulfonates
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000005649 metathesis reaction Methods 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title abstract description 162
- -1 C12 amide Chemical class 0.000 claims abstract description 136
- 239000002253 acid Substances 0.000 claims abstract description 62
- 150000002148 esters Chemical class 0.000 claims abstract description 53
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 31
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 30
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 150000001412 amines Chemical class 0.000 claims description 49
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 45
- 229960003237 betaine Drugs 0.000 claims description 45
- 235000012424 soybean oil Nutrition 0.000 claims description 35
- 239000003549 soybean oil Substances 0.000 claims description 35
- 239000004094 surface-active agent Substances 0.000 claims description 32
- 150000002194 fatty esters Chemical class 0.000 claims description 27
- 150000003871 sulfonates Chemical class 0.000 claims description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- 150000004665 fatty acids Chemical class 0.000 claims description 19
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 17
- 235000019482 Palm oil Nutrition 0.000 claims description 15
- 239000002540 palm oil Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000013527 degreasing agent Substances 0.000 claims description 12
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 10
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 10
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 10
- 239000000872 buffer Substances 0.000 claims description 8
- 239000005630 Diquat Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000003599 detergent Substances 0.000 claims description 7
- 239000007844 bleaching agent Substances 0.000 claims description 6
- 239000003752 hydrotrope Substances 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 239000003082 abrasive agent Substances 0.000 claims description 3
- 150000001470 diamides Chemical class 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 abstract description 44
- 239000000047 product Substances 0.000 description 72
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 69
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 65
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 52
- 239000003921 oil Substances 0.000 description 51
- 235000019198 oils Nutrition 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 48
- 238000000034 method Methods 0.000 description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 150000001336 alkenes Chemical class 0.000 description 36
- 0 C*(C)(CCCNC(CCCCCCCC=C)=O)CC(CS(O)(=O)=O)O Chemical compound C*(C)(CCCNC(CCCCCCCC=C)=O)CC(CS(O)(=O)=O)O 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 30
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 29
- 150000001408 amides Chemical class 0.000 description 29
- 150000004702 methyl esters Chemical class 0.000 description 27
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 26
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
- 229940117986 sulfobetaine Drugs 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical class CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 20
- 238000005686 cross metathesis reaction Methods 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- DUWQEMMRMJGHSA-UHFFFAOYSA-N methyl dodec-9-enoate Chemical compound CCC=CCCCCCCCC(=O)OC DUWQEMMRMJGHSA-UHFFFAOYSA-N 0.000 description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- SBIGSHCJXYGFMX-UHFFFAOYSA-N methyl dec-9-enoate Chemical compound COC(=O)CCCCCCCC=C SBIGSHCJXYGFMX-UHFFFAOYSA-N 0.000 description 17
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 16
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 238000007792 addition Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000004817 gas chromatography Methods 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 11
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 125000005907 alkyl ester group Chemical group 0.000 description 10
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 10
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 10
- 238000005872 self-metathesis reaction Methods 0.000 description 10
- 229940001584 sodium metabisulfite Drugs 0.000 description 10
- 235000010262 sodium metabisulphite Nutrition 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- 238000004140 cleaning Methods 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- HGGLIXDRUINGBB-ONEGZZNKSA-N dimethyl (e)-octadec-9-enedioate Chemical compound COC(=O)CCCCCCC\C=C\CCCCCCCC(=O)OC HGGLIXDRUINGBB-ONEGZZNKSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 238000006277 sulfonation reaction Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003626 triacylglycerols Chemical class 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 7
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- UVUVJPNGAPWYQP-SNAWJCMRSA-N CC/C=C/CCCCCCCC(=O)OCCOC Chemical compound CC/C=C/CCCCCCCC(=O)OCCOC UVUVJPNGAPWYQP-SNAWJCMRSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 150000001298 alcohols Polymers 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- IZFGRAGOVZCUFB-UHFFFAOYSA-N methyl hexadec-9-enoate Chemical compound CCCCCCC=CCCCCCCCC(=O)OC IZFGRAGOVZCUFB-UHFFFAOYSA-N 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 150000003512 tertiary amines Chemical group 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000012972 dimethylethanolamine Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000011984 grubbs catalyst Substances 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000005956 quaternization reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- BGDSSPPOJPLLRI-UHFFFAOYSA-N C=CCCCCCCCC(=O)OCCOC Chemical compound C=CCCCCCCCC(=O)OCCOC BGDSSPPOJPLLRI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000002193 fatty amides Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KAESGLRKBHDZRZ-AATRIKPKSA-N CC/C=C/CCCCCCCC(=O)NCCC[N+](C)(C)CC(O)CS(=O)(=O)[O-] Chemical compound CC/C=C/CCCCCCCC(=O)NCCC[N+](C)(C)CC(O)CS(=O)(=O)[O-] KAESGLRKBHDZRZ-AATRIKPKSA-N 0.000 description 3
- XKFMYLKINQBQMQ-UHFFFAOYSA-M CCCC(CCCCCCCC(=O)NCCC[N+](C)(C)CC(=O)[O-])S(=O)(=O)O[Na] Chemical compound CCCC(CCCCCCCC(=O)NCCC[N+](C)(C)CC(=O)[O-])S(=O)(=O)O[Na] XKFMYLKINQBQMQ-UHFFFAOYSA-M 0.000 description 3
- PTHYIABNEJKIFA-UHFFFAOYSA-N CN(C)C(=O)CCCCCCCCC[Na].O=S(=O)=O Chemical compound CN(C)C(=O)CCCCCCCCC[Na].O=S(=O)=O PTHYIABNEJKIFA-UHFFFAOYSA-N 0.000 description 3
- CFQAEFSYHXQCEP-ONEGZZNKSA-N COCCOC(=O)CCCCCCC/C=C/CCCCCCCC(=O)OCCOC Chemical compound COCCOC(=O)CCCCCCC/C=C/CCCCCCCC(=O)OCCOC CFQAEFSYHXQCEP-ONEGZZNKSA-N 0.000 description 3
- FXCUGNIFFYAEMQ-UHFFFAOYSA-N COCCOC(=O)CCCCCCCCC[Na].O=S(=O)=O Chemical compound COCCOC(=O)CCCCCCCCC[Na].O=S(=O)=O FXCUGNIFFYAEMQ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
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- 238000004508 fractional distillation Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229940073769 methyl oleate Drugs 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 2
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- SBLKVIQSIHEQOF-UHFFFAOYSA-N octadec-9-enedioic acid Chemical compound OC(=O)CCCCCCCC=CCCCCCCCC(O)=O SBLKVIQSIHEQOF-UHFFFAOYSA-N 0.000 description 1
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- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
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- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
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- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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- C11D1/92—Sulfobetaines ; Sulfitobetaines
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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- C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
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- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
Definitions
- the invention relates to hard surface cleaners, and particularly to compositions useful therein as surfactants or solvents that derive from natural oil metathesis.
- Hard surface cleaners continuously evolve and adapt to customer demands, changing times, and increasingly strict health and environmental regulations.
- Successful hard surface cleaners can remove greasy dirt from smooth or highly polished surfaces and disinfect them without leaving behind noticeable films or streaks.
- Modern aqueous cleaners designed primarily for home or institutional use, typically include one or more surfactants in addition to water.
- the cleaners include a small proportion of low-toxicity organic solvent(s), antimicrobial agents, buffers, sequestering agents, builders, bleaching agents, hydrotropes, and other components.
- As formulators seek to create more environmentally friendly products they often reduce the amount of solvent(s), bring pH closer to neutral (5-9), and choose builders/buffers such as organic acid salts (citrate) that generally have lower performance than phosphates or EDTA.
- 6,284,723 antimicrobial formulation comprising an amine oxide and a quaternary ammonium surfactant
- U.S. Pat. No. 6,399,553 anionic surfactant mixture comprising an alkyl diphenyloxide disulfonate and an alkane sulfonate
- U.S. Pat. No. 6,511,953 bleaching agent, buffer to maintain pH at least 11.5, and a surfactant mixture comprising an ethoxylated nonionic surfactant and an anionic surfactant
- hard-surface cleaners have been formulated to contain fatty esters or amides made by hydrolysis or transesterification of triglycerides, which are typically animal or vegetable fats. Consequently, the fatty portion of the acid or ester will typically have 6-22 carbons with a mixture of saturated and internally unsaturated chains. Depending on source, the fatty acid or ester often has a preponderance of C 16 to C 22 component.
- methanolysis of soybean oil provides the saturated methyl esters of palmitic (C 16 ) and stearic (C 18 ) acids and the unsaturated methyl esters of oleic (C 18 mono-unsaturated), linoleic (C 18 di-unsaturated), and ⁇ -linolenic (C 18 tri-unsaturated) acids.
- These materials are generally less than completely satisfactory, however, because compounds having such large carbon chains can behave functionally as soil under some cleaning conditions.
- Recent improvements in metathesis catalysts provide an opportunity to generate reduced chain length, monounsaturated feedstocks, which are valuable for making detergents and surfactants, from C 16 to C 22 -rich natural oils such as soybean oil or palm oil.
- Soybean oil and palm oil can be more economical than, for example, coconut oil, which is a traditional starting material for making detergents.
- metathesis relies on conversion of olefins into new products by rupture and reformation of carbon-carbon double bonds mediated by transition metal carbene complexes.
- Self-metathesis of an unsaturated fatty ester can provide an equilibrium mixture of starting material, an internally unsaturated hydrocarbon, and an unsaturated diester.
- methyl oleate(methyl cis-9-octadecenoate) is partially converted to 9-octadecene and dimethyl 9-octadecene-1,18-dioate, with both products consisting predominantly of the trans-isomer.
- Metathesis effectively isomerizes the cis-double bond of methyl oleate to give an equilibrium mixture of cis- and trans-isomers in both the “unconverted” starting material and the metathesis products, with the trans-isomers predominating.
- Cross-metathesis of unsaturated fatty esters with olefins generates new olefins and new unsaturated esters that can have reduced chain length and that may be difficult to make otherwise.
- cross-metathesis of methyl oleate and 3-hexene provides 3-dodecene and methyl 9-dodecenoate (see also U.S. Pat. No. 4,545,941).
- Terminal olefins are particularly desirable synthetic targets, and Elevance Renewable Sciences, Inc. recently described an improved way to prepare them by cross-metathesis of an internal olefin and an ⁇ -olefin in the presence of a ruthenium alkylidene catalyst (see U.S. Pat. Appl. Publ.
- the feedstocks which include metathesis-derived C 10 -C 17 monounsaturated acids, octadecene-1,18-dioic acid, and their ester derivatives, preferably have at least 1 mole % of trans- ⁇ 9 unsaturation. Because performance of a particular surfactant or blend of surfactants in a hard surface cleaner is not easily inferred from surfactant structure, we performed extensive experimental investigations to identify subclasses of surfactants having desirable attributes for use in hard surface cleaners.
- New surfactant classes are always of interest to formulators of hard surface cleaners.
- Surfactants based on renewable resources will continue to be in demand as alternatives to petroleum-based surfactants.
- Traditional natural sources of fatty acids and esters used for making surfactants generally have predominantly (or exclusively) cis-isomers and lack relatively short-chain (e.g., C 10 or C 12 ) unsaturated fatty portions.
- Metathesis chemistry provides an opportunity to generate precursors having shorter chains and mostly trans-isomers, which could impart improved performance when the precursors are converted to downstream compositions (e.g., in surfactants).
- Formulators will benefit from identification of particular subclasses of surfactants that derive from renewable sources and have desirable attributes for hard surface cleaners.
- the invention relates to hard surface cleaners comprising at least one anionic surfactant derived from a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives.
- the anionic surfactant is selected from C 10 , C 12 , C 16 , or C 18 sulfonates, C 10 amide sulfonates, sulfonated C 10 fatty ester alkoxylates, sulfonated C 12 mid-EO fatty ester alkoxylates, C 12 amidoamine sulfonates, C 12 or C 18 amidoamine betaine sulfonates, C 10 , C 12 , C 16 , or C 18 amidoamine oxide sulfonates, sulfonated C 18 low-EO fatty ester alkoxylates, C 18 diamidoamine sulfonates, C 18 amidoamine dibetaine sulfonates, C 18 amidoamine diquat sulfonates, sulfo-estolides of C 10 unsaturated fatty acids and C 10 or C 18 saturated fatty acids, sulfo-estolides of C 10 or C 12 unsaturated fatty esters and C
- the invention relates to hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives.
- the nonionic or amphoteric surfactant is selected from C 10 or C 12 amides, C 10 , C 12 , or C 18 imidazoline quat sulfonates, C 10 or C 12 mid- or high-EO fatty ester alkoxylates, C 10 amine oxides, C 10 betaines, C 10 and C 12 sulfobetaines, C 12 amidoamine sulfobetaines, C 10 or C 12 amidoamine quat sulfonates, C 16 amidoamines, C 16 amidoamine betaines, C 18 mid- or high-EO ethoxylates, C 18 amidoamine monobetaines, C 18 amidoamine dibetaines, C 18 amidoamine monobetaine oxides, C 18 amidoamine monobetaine quats, C 18 amidoamine monobetaine esters, C 18 amidoamine oxide carboxylates, C 18 esteramines, C 18 diamides, amidoamine sulfobetaines made from cross-metathesized
- the invention includes industrial degreasers comprising at least one solvent derived from a metathesis-derived C 10 -C 17 monounsaturated acid and selected from C 10 or C 12 amides.
- industrial degreasers comprising at least one solvent derived from a metathesis-derived C 10 -C 17 monounsaturated acid and selected from C 10 or C 12 amides.
- the C 10 or C 12 amides are superior to commercial standards, neat or diluted, in a test designed to measure the suitability of a solvent for use in an industrial degreaser.
- Hard surface cleaners of the invention include a surfactant derived from natural oil metathesis.
- this surfactant is anionic; in others, it is nonionic or amphoteric.
- These hard surface cleaners comprise at least one anionic surfactant derived from metathesis of a natural oil.
- the cleaners also include one or more other components, e.g., water, an organic solvent, and a nonionic or amphoteric surfactant.
- the amount of water used is typically in the range of 50 to 99 wt. %, preferably from 70 to 98 wt. %, and more preferably from 80 to 96 wt. %.
- the hard surface cleaner is supplied or sold as a concentrate and contains the minimum amount of water needed to solubilize the components. The formulator or even the ultimate customer may dilute the concentrate with water for normal use.
- Suitable organic solvents are described below. They are typically used in an amount within the range of 0.5 to 20 wt. %, preferably from 1 to 10 wt. %, and more preferably from 3 to 8 wt. %.
- a conventional nonionic or amphoteric surfactant can be included. Suitable amphoteric and nonionic surfactants for use in these formulations are summarized further below.
- the amount of nonionic or amphoteric surfactant is typically within the range of 0.1 to 10 wt. %, preferably from 0.2 to 5 wt. %, and more preferably from 0.3 to 2 wt. %.
- a nonionic or amphoteric surfactant derived from natural oil metathesis can be used in addition to or instead of the conventional nonionic or amphoteric surfactant.
- An anionic surfactant derived from metathesis of a natural oil is included. However, not all such compositions are suitable for use. Through extensive experimentation, we identified particular classes of compositions that perform as well or better than commercial anionic surfactants in hard surface cleaners.
- suitable anionic surfactants derive from a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and are selected from C 10 , C 12 , C 16 , or C 18 sulfonates, C 10 amide sulfonates, sulfonated C 10 fatty ester alkoxylates, sulfonated C 12 mid-EO fatty ester alkoxylates, C 12 amidoamine sulfonates, C 12 or C 18 amidoamine betaine sulfonates, C 10 , C 12 , C 16 , or C 18 amidoamine oxide sulfonates, sulfonated C 18 low-EO fatty ester alkoxylates, C 18 diamidoamine sulfonates, C 18 amidoamine dibetaine sulfonates, C 18 amidoamine diquat sulfonates, sulf
- low-EO alkoxylates have an average of 0.5 to 5 EO units
- mid-EO alkoxylates have an average of 5 to 15 EO units
- high-EO alkoxylates have an average of 15 to 50 EO units.
- products made in accordance with the invention are typically mixtures of cis- and trans-isomers. Except as otherwise indicated, all of the structural representations provided herein show only a trans-isomer. The skilled person will understand that this convention is used for convenience only, and that a mixture of cis- and trans-isomers is understood unless the context dictates otherwise. (The “C18-” series of products in the examples below, for instance, are nominally 100% trans-isomers whereas the “Mix-” series are nominally 80:20 trans-/cis-isomer mixtures.) Structures shown often refer to a principal product that may be accompanied by a lesser proportion of other components or positional isomers.
- reaction products from modified triglycerides are complex mixtures.
- sulfonation or sulfitation processes often give mixtures of sultones, alkanesulfonates, and alkenesulfonates, in addition to isomerized products.
- the structures provided represent likely or predominant products. Charges may or may not be shown but are understood, as in the case of amine oxide structures. Counterions, as in quaternized compositions, are not usually included, but they are understood by the skilled person from the context.
- the anionic surfactant is preferably selected from C 12 amidoamine betaine sulfonates and sulfo-estolides of C 10 unsaturated fatty acids and C 18 saturated fatty acids.
- the anionic surfactant is a C 12 amidoamine betaine sulfonate.
- C 12 amidoamine betaine sulfonate These compounds are conveniently made be reacting a metathesis-derived C 12 monounsaturated methyl ester with DMAPA, followed by conversion to a betaine with sodium monochloroacetate under basic conditions, followed by sulfitation.
- a particularly preferred C 12 amidoamine betaine sulfonate has the structure:
- the anionic surfactant is a sulfo-estolide of a C 10 unsaturated fatty acid and a C 18 saturated fatty acid. These are conveniently made by sulfonating a mixture comprising a C 10 unsaturated fatty acid and a C 18 saturated fatty acid, followed by neutralization.
- a particularly preferred sulfo-estolide has the structure:
- the amount of anionic surfactant used is typically within the range of 0.1 to 10 wt. %, preferably from 0.2 to 5 wt. %, and more preferably from 0.3 to 2 wt. %.
- the cleaners identified above rival or outperform commercial baselines in a Gardner straight-line washability test.
- the anionic surfactant derives from metathesis of a natural oil. It is used as a replacement for a commercial anionic surfactant, Stepanol® WA-Extra PCK (sodium lauryl sulfate) in a formulation that also includes water, organic solvent, and nonionic surfactant.
- Stepanol® WA-Extra PCK sodium lauryl sulfate
- the C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives used as a reactant is derived from metathesis of a natural oil.
- these materials particularly the short-chain acids and derivatives (e.g., 9-decylenic acid or 9-dodecylenic acid) have been difficult to obtain except in lab-scale quantities at considerable expense.
- these acids and their ester derivatives are now available in bulk at reasonable cost.
- the C 10 -C 17 monounsaturated acids and esters are conveniently generated by cross-metathesis of natural oils with olefins, preferably ⁇ -olefins, and particularly ethylene, propylene, 1-butene, 1-hexene, 1-octene, and the like.
- Self-metathesis of the natural oil or a C 10 acid or ester precursor e.g., methyl 9-decenoate
- At least a portion of the C 10 -C 17 monounsaturated acid has “ ⁇ 9 ” unsaturation, i.e., the carbon-carbon double bond in the C 10 -C 17 acid is at the 9-position with respect to the acid carbonyl.
- an alkyl chain of 1 to 7 carbons, respectively is attached to C10.
- the unsaturation is at least 1 mole % trans- ⁇ 9 , more preferably at least 25 mole % trans- ⁇ 9 , more preferably at least 50 mole % trans- ⁇ 9 , and even more preferably at least 80% trans- ⁇ 9 .
- the unsaturation may be greater than 90 mole %, greater than 95 mole %, or even 100% trans- ⁇ 9 .
- naturally sourced fatty acids that have ⁇ 9 unsaturation e.g., oleic acid, usually have ⁇ 100% cis-isomers.
- trans-geometry particularly trans- ⁇ 9 geometry
- the skilled person will recognize that the configuration and the exact location of the carbon-carbon double bond will depend on reaction conditions, catalyst selection, and other factors. Metathesis reactions are commonly accompanied by isomerization, which may or may not be desirable. See, for example, G. Djigoué and M. Meier, Appl. Catal. A: General 346 (2009) 158, especially FIG. 3.
- the skilled person might modify the reaction conditions to control the degree of isomerization or alter the proportion of cis- and trans-isomers generated. For instance, heating a metathesis product in the presence of an inactivated metathesis catalyst might allow the skilled person to induce double bond migration to give a lower proportion of product having trans- ⁇ 9 geometry.
- trans-isomer content (relative to the usual all-cis configuration of the natural monounsaturated acid or ester) imparts different physical properties to surfactant compositions made from them, including, for example, modified physical form, melting range, compactability, and other important properties. These differences should allow formulators that use surfactants greater latitude or expanded choice as they use them in cleaners, fabric treatment, personal care, agricultural uses, and other end uses, particularly hard surface cleaners.
- Suitable metathesis-derived C 10 -C 17 monounsaturated acids include, for example, 9-decylenic acid (9-decenoic acid), 9-undecenoic acid, 9-dodecylenic acid (9-dodecenoic acid), 9-tridecenoic acid, 9-tetradecenoic acid, 9-pentadecenoic acid, 9-hexadecenoic acid, 9-heptadecenoic acid, and the like, and their ester derivatives.
- cross-metathesis or self-metathesis of the natural oil is followed by separation of an olefin stream from a modified oil stream, typically by distilling out the more volatile olefins.
- the modified oil stream is then reacted with a lower alcohol, typically methanol, to give glycerin and a mixture of alkyl esters.
- This mixture normally includes saturated C 6 -C 22 alkyl esters, predominantly C 16 -C 18 alkyl esters, which are essentially spectators in the metathesis reaction.
- the rest of the product mixture depends on whether cross- or self-metathesis is used.
- the alkyl ester mixture will include a C 18 unsaturated diester.
- the resulting alkyl ester mixture includes a C 10 unsaturated alkyl ester and one or more C 11 to C 17 unsaturated alkyl ester coproducts in addition to the glycerin by-product.
- the terminally unsaturated C 10 product is accompanied by different coproducts depending upon which ⁇ -olefin(s) is used as the cross-metathesis reactant.
- 1-butene gives a C 12 unsaturated alkyl ester
- 1-hexene gives a C 14 unsaturated alkyl ester, and so on.
- the C 10 unsaturated alkyl ester is readily separated from the C 11 to C 17 unsaturated alkyl ester and each is easily purified by fractional distillation.
- These alkyl esters are excellent starting materials for making the inventive hard surface cleaners.
- Natural oils suitable for use as a feedstock to generate the C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives from self-metathesis or cross-metathesis with olefins are well known.
- suitable natural oils include vegetable oils, algal oils, animal fats, tall oils, derivatives of the oils, and combinations thereof.
- suitable natural oils include, for example, soybean oil, palm oil, rapeseed oil, coconut oil, palm kernel oil, sunflower oil, safflower oil, sesame oil, corn oil, olive oil, peanut oil, cottonseed oil, canola oil, castor oil, tallow, lard, poultry fat, fish oil, and the like.
- Soybean oil, palm oil, rapeseed oil, and mixtures thereof are preferred natural oils.
- Natural oils e.g., high-oleate soybean oil or genetically modified algal oil
- Preferred natural oils have substantial unsaturation, as this provides a reaction site for the metathesis process for generating olefins.
- Particularly preferred are natural oils that have a high content of unsaturated fatty groups derived from oleic acid.
- particularly preferred natural oils include soybean oil, palm oil, algal oil, and rapeseed oil.
- a modified natural oil such as a partially hydrogenated vegetable oil, can be used instead of or in combination with the natural oil.
- a natural oil is partially hydrogenated, the site of unsaturation can migrate to a variety of positions on the hydrocarbon backbone of the fatty ester moiety. Because of this tendency, when the modified natural oil is self-metathesized or is cross-metathesized with the olefin, the reaction products will have a different and generally broader distribution compared with the product mixture generated from an unmodified natural oil. However, the products generated from the modified natural oil are similarly converted to anionic surfactant compositions for the hard surface cleaners.
- An alternative to using a natural oil as a feedstock to generate the C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives from self-metathesis or cross-metathesis with olefins is a monounsaturated fatty acid obtained by the hydrolysis of a vegetable oil or animal fat, or an ester or salt of such an acid obtained by esterification of a fatty acid or carboxylate salt, or by transesterification of a natural oil with an alcohol. Also useful as starting compositions are polyunsaturated fatty esters, acids, and carboxylate salts.
- the salts can include an alkali metal (e.g., Li, Na, or K); an alkaline earth metal (e.g., Mg or Ca); a Group 13-15 metal (e.g., B, Al, Sn, Pb, or Sb), or a transition, lanthanide, or actinide metal. Additional suitable starting compositions are described at pp. 7-17 of PCT application WO 2008/048522, the contents of which are incorporated by reference herein.
- the other reactant in the cross-metathesis reaction is an olefin.
- Suitable olefins are internal or ⁇ -olefins having one or more carbon-carbon double bonds. Mixtures of olefins can be used.
- the olefin is a monounsaturated C 2 -C 10 ⁇ -olefin, more preferably a monounsaturated C 2 -C 8 ⁇ -olefin.
- Preferred olefins also include C 4 -C 9 internal olefins.
- suitable olefins for use include, for example, ethylene, propylene, 1-butene, cis- and trans-2-butene, 1-pentene, isohexylene, 1-hexene, 3-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, and the like, and mixtures thereof.
- Cross-metathesis is accomplished by reacting the natural oil and the olefin in the presence of a homogeneous or heterogeneous metathesis catalyst.
- the olefin is omitted when the natural oil is self-metathesized, but the same catalyst types are generally used.
- Suitable homogeneous metathesis catalysts include combinations of a transition metal halide or oxo-halide (e.g., WOCl 4 or WCl 6 ) with an alkylating cocatalyst (e.g., Me 4 Sn).
- Preferred homogeneous catalysts are well-defined alkylidene (or carbene) complexes of transition metals, particularly Ru, Mo, or W.
- Second-generation Grubbs catalysts also have the general formula described above, but L 1 is a carbene ligand where the carbene carbon is flanked by N, O, S, or P atoms, preferably by two N atoms. Usually, the carbene ligand is party of a cyclic group. Examples of suitable second-generation Grubbs catalysts also appear in the '086 publication.
- L 1 is a strongly coordinating neutral electron donor as in first- and second-generation Grubbs catalysts
- L 2 and L 3 are weakly coordinating neutral electron donor ligands in the form of optionally substituted heterocyclic groups.
- L 2 and L 3 are pyridine, pyrimidine, pyrrole, quinoline, thiophene, or the like.
- a pair of substituents is used to form a bi- or tridentate ligand, such as a biphosphine, dialkoxide, or alkyldiketonate.
- Grubbs-Hoveyda catalysts are a subset of this type of catalyst in which L 2 and R 2 are linked. Typically, a neutral oxygen or nitrogen coordinates to the metal while also being bonded to a carbon that is ⁇ -, ⁇ -, or ⁇ - with respect to the carbene carbon to provide the bidentate ligand. Examples of suitable Grubbs-Hoveyda catalysts appear in the '086 publication.
- Heterogeneous catalysts suitable for use in the self- or cross-metathesis reaction include certain rhenium and molybdenum compounds as described, e.g., by J. C. Mol in Green Chem. 4 (2002) 5 at pp. 11-12.
- catalyst systems that include Re 2 O 7 on alumina promoted by an alkylating cocatalyst such as a tetraalkyl tin lead, germanium, or silicon compound.
- Others include MoCl 3 or MoCl 5 on silica activated by tetraalkyltins.
- the metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are converted to particular subclasses of sulfonates, amide sulfonates, sulfonated fatty ester alkoxylates, amidoamine sulfonates, amidoamine betaine sulfonates, amidoamine oxide sulfonates, sulfo-estolides, and other compositions that are useful as anionic surfactants in hard surface cleaners.
- General synthetic procedures for making these compositions are provided below (General procedures A-L) and are summarized for each particular composition prepared in Tables 2A and 2B.
- amidoamine sulfonate C12-42 is conveniently made using Methods E and J by reacting methyl 9-dodecenoate with DMAPA to make the DMAPA amide, followed by sulfitation of the internal double bond to give the amidoamine sulfonate.
- the hard surface cleaner can include additional conventional components.
- the cleaners include one or more additives such as builders, buffers, abrasives, electrolytes, bleaching agents, fragrances, dyes, foaming control agents, antimicrobial agents, thickeners, pigments, gloss enhancers, enzymes, detergents, surfactants, cosolvents, dispersants, polymers, silicones, hydrotropes, and the like.
- These hard surface cleaners comprise at least one nonionic or amphoteric surfactant derived from metathesis of a natural oil.
- the cleaners include one or more other components, including water, an organic solvent, an anionic surfactant, and the like.
- the amount of water used is typically in the range of 50 to 99 wt. %, preferably from 70 to 98 wt. %, and more preferably from 80 to 96 wt. %.
- Suitable organic solvents are described below. They are typically used in an amount within the range of 0.5 to 20 wt. %, preferably from 1 to 10 wt. %, and more preferably from 3 to 8 wt. %.
- a conventional anionic surfactant can be included. Suitable anionic surfactants for use in these formulations are summarized further below.
- the amount anionic surfactant used is typically within the range of 0.1 to 10 wt. %, preferably from 0.2 to 5 wt. %, and more preferably from 0.3 to 2 wt. %.
- an anionic surfactant derived from natural oil metathesis can be used in addition to or instead of the conventional anionic surfactant.
- a nonionic or amphoteric surfactant derived from metathesis of a natural oil is included. However, not all such compositions are suitable for use. Through extensive experimentation, we identified particular classes of compositions that perform as well or better than commercial anionic surfactants in hard surface cleaners.
- suitable nonionic or amphoteric surfactants derive from a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and are selected from C 10 or C 12 amides, C 10 , C 12 , or C 18 imidazoline quat sulfonates, C 10 or C 12 mid- or high-EO fatty ester alkoxylates, C 10 amine oxides, C 10 betaines, C 10 and C 12 sulfobetaines, C 12 amidoamine sulfobetaines, C 10 or C 12 amidoamine quat sulfonates, C 16 amidoamines, C 16 amidoamine betaines, C 18 mid- or high-EO ethoxylates, C 18 amidoamine monobetaines, C 18 amidoamine dibetaines, C 18 amidoamine monobetaine oxides, C 18 amidoamine monobetaine quats, C 18 amido
- nonionic or amphoteric surfactants include quaternized C 12 imidazoline sulfonates, C 10 high-EO fatty ester alkoxylates, C 12 amidoamine sulfobetaines, C 10 quaternized amidoamine sulfonates, and amidoamine sulfobetaines made from cross-metathesized soybean oil.
- the nonionic or amphoteric surfactant is a quaternized C 12 imidazoline sulfonate.
- These compounds are conveniently made by reacting a metathesis-derived C 12 monounsaturated methyl ester with DETA to give the an amide intermediate, followed by acid-catalyzed ring closure to the imidazoline, followed by sulfitation of the olefin.
- a particularly preferred example has the structure:
- the nonionic or amphoteric surfactant is a C 10 high-EO fatty ester alkoxylate. Reaction of a metathesis-derived fatty methyl ester with EO in the presence of an insertion catalyst readily provides the alkoxylate.
- One preferred example has the structure:
- n the average number of oxyethylene units, has a value within the range of 15 to 50.
- the nonionic or amphoteric surfactant is a C 12 amidoamine sulfobetaine.
- These compounds can be prepared by reacting a metathesis-derived fatty methyl ester with DMAPA, followed by conversion of the tertiary amine group to a sulfobetaine.
- the fatty DMAPA amine is reacted, for example, with the reaction product of epichlorohydrin and sodium metabisulfite.
- the nonionic or amphoteric surfactant is a C 10 quaternized amidoamine sulfonate.
- Suitable compositions of this type can be made by reacting a metathesis-derived C 10 methyl ester with DMAPA, followed by quaternization of the tertiary amine with dimethyl sulfate, followed by sulfitation of the olefin.
- One preferred example has the structure:
- the amount of nonionic or amphoteric surfactant used is typically within the range of 0.1 to 10 wt. %, preferably from 0.2 to 5 wt. %, and more preferably from 0.3 to 2 wt. %.
- the aqueous cleaners identified above rival or outperform commercial baselines in a Gardner straight-line washability test.
- the nonionic or amphoteric surfactant derives from metathesis of a natural oil. It is used in a formulation that also includes water, organic solvent, and an anionic surfactant.
- the control sample omits the test composition. We found that only certain subclasses of tested compositions performed as well or better than the control in the washability test (see Table 6), while other compositions, often structurally similar, performed poorly in this test (see Table 7).
- the C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives used to make the anionic surfactant come from natural oil metathesis as is detailed fully above.
- the feedstocks are converted to particular subclasses of amides, quaternized imidazoline sulfonates, fatty ester alkoxylates, amine oxides, betaines, amidoamine sulfobetaines, quaternized amidoamine sulfonates, amidoamine monobetaines, amidoamine monobetaine oxides, amidoamine sulfobetaines made from cross-metathesized palm or soybean oil or from self-metathesized soybean oil, amidoamine betaines made from cross-metathesized or self-metathesized soybean oil, amidoamine oxides made from cross-metathesized soybean oil, and other compositions that are useful as nonionic or amphoteric surfactants in hard surface cleaners
- amine oxide C10-39 is conveniently made using Methods E, G, and D by reacting methyl 9-dodecenoate with dimethylamine (DMA) to make the amide, followed by reduction of the amide to an amine with lithium aluminum hydride, followed by oxidation of the amine with hydrogen peroxide to give the amine oxide.
- DMA dimethylamine
- the hard surface cleaner can include the additional conventional components (builders, buffers, etc.) noted earlier.
- aqueous hard surface cleaners can contain the following components:
- An organic solvent preferably a water-soluble one, can be included in the hard surface cleaners.
- Preferred solvents include alcohols, glycols, glycol ethers, glycol ether esters, amides, esters, and the like. Examples include C 1 -C 6 alcohols, C 1 -C 6 diols, C 3 -C 24 glycol ethers, and mixtures thereof.
- Suitable alcohols include, for example, methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 1-pentanol, 1-hexanol, amyl alcohol, and mixtures thereof.
- Suitable glycol ethers include, e.g., ethylene glycol n-butyl ether, ethylene glycol n-propyl ether, propylene glycol methyl ether, propylene glycol n-propyl ether, propylene glycol tert-butyl ether, propylene glycol n-butyl ether, diethylene glycol n-butyl ether, dipropylene glycol methyl ether, and the like, and mixtures thereof.
- Suitable glycol ether esters include, for example, propylene glycol methyl ether acetate, propylene glycol n-butyl ether acetate, and the like.
- Anionic surfactants generally have a molecular weight below 10,000 and comprise one or more functional groups that exhibit a net anionic charge when in aqueous solution.
- Suitable anionic surfactants include fatty alkyl sulfates, fatty alkyl ether sulfates, paraffin sulfonates, olefin sulfonates, alkyl aryl sulfonates, alkyl ester sulfonates, fatty ester sulfonates, sulfosuccinate esters, organic phosphates, alkyl alkoxylated sulfates, and the like.
- anionic surfactants are described in U.S. Pat. Nos. 3,929,678, 5,929,022, 6,399,553, 6,489,285, 6,511,953, 6,949,498, and U.S. Pat. Appl. Publ. No. 2010/0184855, the teachings of which are incorporated herein by reference.
- Nonionic surfactants typically function as wetting agents, hydrotropes, and/or couplers.
- Suitable nonionic surfactants include, for example, fatty alcohols, alcohol fatty esters, fatty alcohol ethoxylates, alkylphenol ethoxylates, alkoxylate block copolymers, alkoxylated fatty amides, fatty amides, fatty amine oxides, castor oil alkoxylates, polyol esters, fatty methyl esters, glycerol esters, glycol fatty esters, tallow amine ethoxylates, polyethylene glycol esters, and the like.
- Fatty alcohol ethoxylates are preferred.
- Suitable amphoteric surfactants include, for example, amine oxides, betaines, sulfobetaines, and the like. Specific examples include cocoamidopropylamine oxide, cetamine oxide, lauramine oxide, myristylamine oxide, stearamine oxide, alkyl betaines, cocobetaines, and amidopropyl betaines, (e.g., lauryl betaines, cocoamidopropyl betaines, lauramidopropyl betaines), and combinations thereof.
- the invention relates to solvent-based degreasers intended principally for industrial use.
- These degreasers comprise a C 10 or C 12 amide solvent derived from a metathesis-derived C 10 -C 17 monounsaturated acid or its ester derivative.
- amide solvents are superior to commercial standards when used neat or diluted in removing greasy soils.
- standard soil Gardner ASTM D4488-95 A5
- a drop of test solvent is applied to the tile, and after each 10 seconds (neat samples), or 30 seconds (diluted), a second drop is applied adjacent to the first, and so on.
- the C 10 or C 12 amide solvent derives from a metathesis-derived C 10 -C 17 monounsaturated acid or its ester derivative. Suitable amides are conveniently made by heating a metathesis-derived C 10 or C 12 fatty methyl ester with dimethylamine. Particularly preferred examples have the structure:
- the solvent-based degreaser can be used neat (i.e., at full strength), or it can be diluted with water. Diluted compositions comprise at least 2 wt. % of the degreaser.
- the diluted degreaser comprises from 2 to 20 wt. % of the C 10 or C 12 amide solvent, from 3 to 25 wt. % of a fatty amine oxide, and from 55 to 95 wt. % of water.
- the degreaser can include one or more conventional additives (builders, buffers, bleaching agents, surfactants, cosolvents, etc.) as described above for the aqueous hard surface cleaners.
- a clean, dry, stainless-steel jacketed 5-gallon Parr reactor equipped with a dip tube, overhead stirrer, internal cooling/heating coils, temperature probe, sampling valve, and relief valve is purged with argon to 15 psig.
- the reactor is sealed, and the SBO is purged with argon for 2 h while cooling to 10° C. After 2 h, the reactor is vented to 10 psig.
- the dip tube valve is connected to a 1-butene cylinder (Airgas, CP grade, 33 psig headspace pressure, >99 wt. %) and re-pressurized to 15 psig with 1-butene.
- the reactor is again vented to 10 psig to remove residual argon.
- the SBO is stirred at 350 rpm and 9-15° C. under 18-28 psig 1-butene until 3 mol 1-butene per SBO olefin bond are transferred into the reactor ( ⁇ 2.2 kg 1-butene over 4-5 h).
- a toluene solution of [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-dichlororuthenium(3-methyl-2-butenylidene)(tricyclohexylphosphine) (C827, Materia) is prepared in a Fischer-Porter pressure vessel by dissolving 130 mg catalyst in 30 g of toluene (10 mol ppm per mol olefin bond of SBO).
- the catalyst mixture is added to the reactor via the reactor dip tube by pressurizing the headspace inside the Fischer-Porter vessel with argon to 50-60 psig.
- the Fischer-Porter vessel and dip tube are rinsed with additional toluene (30 g).
- the reaction mixture is stirred for 2.0 h at 60° C. and is then allowed to cool to ambient temperature while the gases in the headspace are vented.
- reaction mixture is transferred to a round-bottom flask containing bleaching clay (Pure-Flo® B80 CG clay, product of Oil-Dri Corporation of America, 2% w/w SBO, 58 g) and a magnetic stir bar.
- bleaching clay Pure-Flo® B80 CG clay, product of Oil-Dri Corporation of America, 2% w/w SBO, 58 g
- the reaction mixture is stirred at 85° C. under argon. After 2 h, during which time any remaining 1-butene is allowed to vent, the reaction mixture cools to 40° C. and is filtered through a glass frit. An aliquot of the product mixture is transesterified with 1% w/w NaOMe in methanol at 60° C. By gas chromatography (GC), it contains: methyl 9-decenoate (22 wt.
- GC gas chromatography
- Example 1A The procedure of Example 1A is generally followed with 1.73 kg SBO and 3 mol 1-butene/SBO double bond. An aliquot of the product mixture is transesterified with sodium methoxide in methanol as described above.
- the products (by GC) are: methyl 9-decenoate (24 wt. %), methyl 9-dodecenoate (18 wt. %), dimethyl 9-octadecenedioate (2 wt. %), and methyl 9-octadecenoate (2 wt. %).
- Example 1A The procedure of Example 1A is generally followed with 1.75 kg SBO and 3 mol 1-butene/SBO double bond. An aliquot of the product mixture is transesterified with sodium methoxide in methanol as described above.
- the products (by GC) are: methyl 9-decenoate (24 wt. %), methyl 9-dodecenoate (17 wt. %), dimethyl 9-octadecenedioate (3 wt. %), and methyl 9-octadecenoate (2 wt. %).
- Example 1A The procedure of Example 1A is generally followed with 2.2 kg SBO and 3 mol 1-butene/SBO double bond. Additionally, the toluene used to transfer the catalyst (60 g) is replaced with SBO. An aliquot of the product mixture is transesterified with sodium methoxide in methanol as described above.
- the products (by GC) are: methyl 9-decenoate (25 wt. %), methyl 9-dodecenoate (18 wt. %), dimethyl 9-octadecenedioate (3 wt. %), and methyl 9-octadecenoate (1 wt. %).
- a 12-L round-bottom flask equipped with a magnetic stir bar, heating mantle, and temperature controller is charged with the combined reaction products from Examples 1A-1D (8.42 kg).
- a cooling condenser with a vacuum inlet is attached to the middle neck of the flask and a receiving flask is connected to the condenser.
- Volatile hydrocarbons (olefins) are removed from the reaction product by vacuum distillation. Pot temperature: 22° C.-130° C.; distillation head temperature: 19° C.-70° C.; pressure: 2000-160 ⁇ torr. After removing the volatile hydrocarbons, 5.34 kg of non-volatile residue remains.
- a 12-L round-bottom flask fitted with a magnetic stir bar, condenser, heating mantle, temperature probe, and gas adapter is charged with sodium methoxide in methanol (1% w/w, 4.0 L) and the non-volatile product mixture produced in Example 1E (5.34 kg).
- a 12-L round-bottom flask fitted with a magnetic stirrer, packed column, and temperature controller is charged with the methyl ester mixture produced in example 1F (5.03 kg), and the flask is placed in a heating mantle.
- the glass column is 2′′ ⁇ 36′′ and contains 0.16′′ Pro-PakTM stainless-steel saddles (Cannon Instrument Co.).
- the column is attached to a fractional distillation head to which a 1-L pre-weighed flask is fitted for collecting fractions. Distillation is performed under vacuum (100-120 ⁇ torr).
- a reflux ratio of 1:3 is used to isolate methyl 9-decenoate (“C10-0”) and methyl 9-dodecenoate (“C12-0”).
- Example 1A The procedures of Example 1A is generally followed except that 1-octene is cross-metathesized with soybean oil instead of 1-butene. Combined reaction products are then stripped as described in Example 1E to remove the more volatile unsaturated hydrocarbon fraction from the modified oil fraction.
- Example 1F The procedure of Example 1F is used to convert the modified oil fraction to a methyl ester mixture that includes methyl 9-hexadecenoate. Fractional distillation at reduced pressure is used to isolate the desired product, methyl 9-hexadecenoate from other methyl esters.
- a sample of unsaturated fatty ester (e.g., 9-decylenic acid methyl ester), is added to methylene chloride in a small-scale batch sulfonation reactor fitted with a dry ice condenser and maintained at around 20° C. with a pre-established 2 L/m flow of N 2 . Additional solvent is used as needed to reduce the viscosity of the reaction mixture.
- sulfur trioxide is evaporated via a 140° C. flash-pot and bubbled through the reactor at a molar ratio of SO 3 to alkene functionality of about 1:1. The addition rate of SO 3 is adjusted to keep the reaction temperature at or below 35° C.
- a tertiary alkanolamine e.g. triethanolamine, N-methyldiethanolamine, N,N-dimethylethanolamine
- an alkoxylated derivative thereof is combined in the same reaction vessel with an ester derivative of 9-decylenic acid, 9-dodecylenic acid, or 9-octadecene-1,18-dioic acid and potassium carbonate.
- This mixture is heated with agitation at a temperature within the range of 150° C. to 200° C.
- the relative amounts of amine and ester (or acid) are balanced to provide the desired stoichiometry taking into account the ester/acid content determined by saponification number.
- the reaction is performed under nitrogen sparge or under vacuum to remove liberated alcohol. When glyceride esters of decylenic acid or dodecylenic acid are used, the liberated glycerin is not removed.
- the reaction is deemed complete when the desired residual amount of starting amine remains.
- Tertiary amines are converted to methyl quats, betaines, or sulfobetaines by reaction with a quaternizing agent.
- the quaternization is performed at temperature within the range of 65° C. to 100° C.
- the quaternizing agent used is dimethyl sulfate for methyl quats, sodium monochloroacetate for betaines, or epichlorohydrin for sulfobetaines.
- the amount of quaternizing agent used is from 0.8 to 1.0 molar equivalents based on the amount of tertiary amine. The reaction is deemed complete when the free amine value is in the desired range as determined by perchloric acid titration.
- a tertiary amine is diluted with water to form a 10-40 wt. % mixture, which is warmed to 50° C. to 75° C. under nitrogen.
- Hydrogen peroxide solution (35% solution, 1 to 2.2 molar eq.) is added dropwise while keeping the temperature below 75° C. The mixture is held at the reaction temperature for 4 to 12 h or until the free peroxide level is below 0.2% as determined by starch iodide paper.
- Unsaturated methyl ester (C 10 , C 12 , or C 16 monoester or C 18 diester) is combined with 1-6 molar equivalents of a primary or secondary amine (e.g., DMA, DEA, MEA, DMAPA).
- a base catalyst e.g., NaOMe or other alkoxide
- the reaction mixture is heated at a temperature within the range of 50° C. to 150° C. until the starting ester is substantially consumed.
- the amide product is purified by distillation, water washing, or other normal means. Alternatively, the product is used “as is” and converted to other derivatives.
- a suitable carboxylic acid is combined with a poly(ethylene glycol)monomethyl ether (0.8-2.5 eq.), an acid catalyst (e.g., sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, or the like), and optionally a solvent (e.g., toluene, xylene, or other hydrocarbons capable of forming a water azeotrope).
- an acid catalyst e.g., sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, or the like
- a solvent e.g., toluene, xylene, or other hydrocarbons capable of forming a water azeotrope.
- the mixture is heated at 120° C. to 180° C. under vacuum, nitrogen sparge, or nitrogen blanket and the liberated water is collected. The reaction continues until the desired acid value is achieved.
- Lithium aluminum hydride (or a similar reducing agent) is dissolved in a solvent (e.g., diethyl ether, THF, dioxane, diglyme) under a nitrogen blanket.
- a suitable fatty amide is dissolved in the same solvent and is added dropwise, keeping the reaction temperature within the range of 25° C. to 50° C. After the addition, the mixture is stirred overnight at room temperature. Water is carefully added to quench the reaction, and aqueous sodium hydroxide is added. The solids are filtered off, and the solvent is removed.
- the amine product is purified by distillation.
- Methyl 9-decenoate or methyl 9-dodecenoate is combined with diethylenetriamine (DETA), with or without a catalyst, in the desired molar ratio of ester groups to primary amino and/or hydroxyl groups.
- DETA diethylenetriamine
- the mixture is heated with agitation to a temperature within the range of 140° C. and 200° C. under a mild vacuum that prevents or minimizes evaporation of DETA from the reaction mixture.
- the reaction proceeds until analysis (IR or 1 H NMR spectroscopy) indicates reasonably complete conversion.
- the contents are then heated at a temperature within the range of 175° C. to 300° C. with a lower vacuum (5-100 mm Hg) to effect ring closure to the imidazoline. Reaction end point is determined by titration.
- a sulfitating agent sodium sulfite, sodium bisulfite, sodium metabisulfite, or the like
- a catalyst peroxides, iron, or other free-radical initiators
- Sulfonation is carried out in a batch reactor maintained at 20° C. under a nitrogen flow (2 L/min.).
- the unsaturated fatty acid or an unsaturated fatty acid and saturated fatty acid mixture is added to methylene chloride.
- Sulfur trioxide is evaporated over 30 min. via a 140° C. flash-pot and is bubbled through the reactor using the nitrogen stream at a molar ratio of SO 3 to alkene functionality of about 1:1.
- the addition rate of SO 3 is adjusted to keep the reaction temperature at or below 35° C.
- the reaction mixture is maintained for an additional 5 min. and the mixture is then concentrated under vacuum.
- the acid product is digested for 1-2 h at 50-85° C. Neutralization is performed using an appropriate base and hydrolysis occurs at 85° C. with the pH maintained with additional base. 1 H NMR is used to determine complete hydrolysis.
- compositions are tested as either an aqueous hard surface cleaner degreaser component or in a non-aqueous degreaser formulation. Unless otherwise indicated below, the compositions are prepared using the general methods summarized in Tables 2A and 2B:
- C10-8 C10 Ethoxylated Fatty Acid Methyl Ester (“eFAME”)
- Methyl ester C10-0 is converted to its respective fatty acid C10-36.
- a mixture of potassium hydroxide in glycerin (16-17 wt. %) is charged to a flask equipped with an overhead stirrer, thermocouple, and nitrogen sparge, and the solution is heated to 100° C.
- the methyl ester is then added.
- An excess of KOH (2 moles per mole of methyl ester) is used.
- the temperature is raised to 140° C. and heating continues until gas chromatography analysis indicates complete conversion.
- Deionized water is added give a weight ratio of product mixture to water of about 1.5.
- the solution is heated to 90° C. to melt any product that may have solidified.
- Aqueous sulfuric acid (30%) is added and mixed, and the layers are allowed to separate. The aqueous layer is drained.
- the fatty acid, C10-36 is washed with deionized water until the aqueous wash is neutral.
- C10-36 fatty acid (45.0 g, 0.256 mol) is charged to a round-bottom flask equipped with an overhead stirrer, Dean-Stark trap, reflux condenser, thermocouple, heating mantle, and temperature controller.
- Polyethylene glycol monomethyl ether (267.0 g, 0.256 mol, an average of about 24 EO units per molecule) and toluene (500 mL) are added.
- the mixture is heated to 124° C. while p-toluenesulfonic acid (3.0 g) is added. Water of reaction begins to collect when the target temperature is reached. After heating 24 h, conversion (by GPC) is 97%.
- the sample is stripped to remove toluene. Residual toluene is removed by stirring at 150° C. under vacuum (1-5 mm Hg) with a low nitrogen sparge.
- a round-bottom flask is charged with methyl ester C10-0 (500 g), DMAPA (331 g), and sodium methoxide/MeOH solution (0.5 wt. % sodium methoxide based on the amount of methyl ester).
- the contents are heated slowly to 140° C. and held for 6 h.
- the reaction mixture is vacuum stripped (110° C. to 150° C.).
- the product, C10-17 is analyzed. Amine value: 224.1 mg KOH/g; iodine value: 102.6 g I 2 /100 g sample; titratable amines: 99.94%.
- amidoamine C10-17 (151.3 g). After warming to 80° C., dimethyl sulfate (68.38 g) is added dropwise. The temperature is raised to 85° C. and the mixture is stirred for 2 h. Isopropyl alcohol (23.45 g) is added, and the mixture stirs for 1 h.
- the product, C10-18, is analyzed: IPA: 7.72 wt. %; pH: 8.41 (1% in 9:1 IPA/water); iodine value: 56.8; tertiary amine: 0.020 meq/g; moisture: 1.7 wt. %; quaternary actives: 91.2 wt. %.
- Methyl quat C10-18 (98.30 g) and water (216.3 g) are charged to a round-bottom flask equipped with stir bar, condenser, and thermocouple. The mixture is heated at 80° C. until homogeneous. Sodium metabisulfite (Na 2 S 2 O 5 ; 23.49 g, 1.03 eq. NaHSO 3 ) is added, and the mixture is held at 80° C. overnight. 1 H NMR (D 2 O) shows ⁇ 50% conversion to the sulfitated product. The mixture is held at 80° C. for 48 h and then reanalyzed; there are no significant changes. Sulfur dioxide is bubbled through the mixture, which is then held at 80° C.
- amidoamine C10-17 60 g
- sodium metabisulfite 25.6 g
- water 114 g
- 50% aq. NaOH 50% aq. NaOH (two 0.3-g portions)
- epichlorohydrin 24.4 g
- Reaction continues at 75° C. for 3 h, and the pH (10% aqueous dilution) is kept between 8.2 and 8.9.
- the mixture cools to room temperature overnight.
- the mixture is reheated to 75° C.
- the pH has fallen to 8.1 and is increased with 50% NaOH (0.3 g).
- Reaction continues for 1 h.
- the reaction is judged complete when the NaCl level stabilizes at 6.55%.
- the mixture cools to room temperature, and the pH is adjusted to 6.95 with 50% H 2 SO 4 .
- the sulfobetaine product, C10-24, is analyzed: NaCl: 6.55 wt. %; solids: 51.8%; sulfobetaine actives (by solids-NaCl): 45.25%.
- 1 H NMR analysis of a dried aliquot of the product mixture supports the proposed structure.
- Methyl ester C10-0 (390.2 g) is charged to a round-bottom flask equipped with an overhead stirrer, and the contents are warmed to 70° C. Potassium hydroxide (16% solution in glycerin, 523 g) is added. The mixture is heated to 100° C. and additional KOH pellets (35.10 g) are added. After stirring 17 h, gas chromatography indicates ⁇ 94% conversion to the fatty acid. Additional KOH (10 g) is added, and stirring continues at 100° C. for 4 h. Conversion by GC is >97%. The mixture stirs at 100° C. for another 4 h, and is then cooled to 80° C.
- the acid product is then digested for 1.5 h at 50° C.
- the acid product is neutralized using water (161.5 g) and 50% aq. NaOH (42.9 g).
- Hydrolysis is carried out at 85° C. Throughout the hydrolysis, a two-phase mixture is present. The mixture cools to room temperature and each phase is analyzed by 1 H NMR. The product is allowed to concentrate in the open air for 2 days. The resulting paste is warmed to 75° C., homogenized by stirring, and cooled to room temperature. Analysis of the sulfo-estolide shows: pH: 7.89 (1% in 9:1 IPA/water); moisture: 23.7 wt. %; inorganic sulfate: 0.94 wt. %; unsulfonated matter: 10.5 wt. %. 1 H NMR analysis supports the proposed composition.
- a flask equipped with nitrogen inlet is charged with sodium metabisulfite (50 g) and water (197 g), and the mixture is warmed to 40° C.
- Aqueous sodium hydroxide (0.6 g of 50% solution) is added.
- epichlorohydrin 47.7 g
- epichlorohydrin 47.7 g
- the mixture is stirred at 70° C. for another 0.5 h.
- More aq. NaOH solution (0.6 g) is added and the mixture stirs briefly.
- Amine C10-38 (90 g) is added, and the temperature is increased to 90° C. After 1 h, the temperature is increased to 95° C. and held at 90-95° C.
- Methyl 9-dodecenoate (“C12-0,” 273.3 g), DABCO (0.3450 g), and DETA (66.48 g) are charged to a round-bottom flask, and the liquid mixture is sparged with nitrogen (175 mL/min). The mixture is heated from 100° C. to 170° C. over 2 h at atmospheric pressure. After 4.5 h at 170° C., a vacuum (90 mm Hg) is applied, and the mixture is heated for an additional 6 h. The resulting distillate (44.3 g) includes about 2 g of DETA. Additional DETA (2 g) is added to the reactor, and heating continues at 170° C. for 5 h at 400 mm Hg. The temperature is raised to 200° C.
- a flask equipped with condenser, nitrogen inlet, thermocouple, and port for an addition flask is charged with imidazoline C12-12 (212.1 g).
- the contents are heated to 80° C., and DMS (59.3 g) is added via the addition flask with a target perchloric acid titer (PAT) value of 0.065.
- PAT perchloric acid titer
- the temperature is raised to 85° C., and stirring continues for 1 h.
- a sample is removed and titrated for PAT (found: 0.045).
- Isopropyl alcohol (30.4 g) is added, and the mixture is stirred for 1 h.
- the product is DETA quat C12-13.
- the C12 DETA quat (C12-13, 126.1 g), IPA (126.1 g), and t-butylperoxybenzoate (2.5 g) are charged to a round-bottom flask. The mixture is heated to 75° C. A solution of sodium metabisulfite (37.5 g), sodium sulfite (7.2 g), deionized water (190.0 g), and t-butylperoxybenzoate (1.2 g) is charged to an addition funnel, and then added dropwise to the reaction mixture, which is held at 75° C. for 16 h. IPA is removed via rotary evaporation. The 1 H NMR spectrum suggests 75% conversion. Moisture content is adjusted to ⁇ 50% by adding water. (Note: the structure indicated above suggests single-site sulfonation, but the skilled person appreciates that at least some of the product with be the result of sulfonation at both carbon-carbon double bonds.)
- a round-bottom flask is charged with methyl 9-dodecenoate (“C12-0,” 670 g). The mixture is stirred mechanically, and DMAPA (387 g) is added. A Dean-Stark trap is fitted to the reactor, and sodium methoxide (30 wt. % solution, 11.2 g) is added. The temperature is raised to 130° C. over 1.5 h, and methanol is collected. After 100 g of distillate is recovered, the temperature is raised to 140° C. and held for 3 h. 1 H NMR shows complete reaction. The mixture is cooled to room temperature overnight. The mixture is then heated to 110° C. and DMAPA is recovered under vacuum. The temperature is slowly raised to 150° C. over 1.5 h and held at 150° C.
- a round-bottom flask is charged with amidoamine C12-17 (210 g) and water (400 g).
- Sodium monochloroacetate (89 g) is added, and the mixture is heated to 80° C.
- the pH is maintained between 8 and 10 with 50% aq. NaOH (measuring pH as a 10% solution in water using pH strips).
- the temperature is raised to 100° C. and held for 4 h.
- the mixture is cooled to room temperature overnight.
- Water (100 g) is added to dilute the mixture, which is reheated to 100° C. for 4 h. Chloride titration shows 5.55% NaCl (expected 5.62%).
- amidoamine C12-17 105 g
- sodium metabisulfite 39.6 g
- water 190 g
- 50% aq. NaOH 50% aq. NaOH
- epichlorohydrin 37.8 g
- Reaction continues at 80° C. for 3.5 h, and the pH (10% aqueous dilution) is kept between 8.2 and 8.6.
- the mixture cools to room temperature overnight.
- the mixture is reheated to 80° C. After 2 h, the pH is 8.5 and the NaCl level is 6.36%.
- the reaction is judged complete.
- the mixture cools to room temperature, and the pH is adjusted to 7.6 with 50% H 2 SO 4 .
- the sulfobetaine product, C12-24, is analyzed: NaCl: 6.34 wt. %; moisture: 49.7%; solids: 50.4%; sulfobetaine actives (by solids-NaCl): 44.0%.
- 1 H NMR analysis of a dried aliquot of the product mixture supports the proposed structure.
- a round-bottom flask is charged with methyl ester feedstock C12-0 (900.0 g, 4.22 mol) and the material is heated to 60° C.
- the reactor is sealed and vacuum is applied for 0.5 h to dry/degas the feedstock.
- the reactor is backfilled with nitrogen, and then sodium methoxide (30 g of 30% solution in methanol) is added via syringe.
- a static vacuum ( ⁇ 30′′ Hg) is established, and then dimethylamine (“DMA,” 190.3 g, 4.22 mol) is slowly added via sub-surface dip tube.
- DMA dimethylamine
- MIX-2 C18 diIPA Ester (80:20 Trans-/Cis-)
- C18-29 C18 DiDMAPA DiAO (100% Trans-)
- MIX-29 C18 DiDMAPA DiAO (80:20 Trans-/Cis-)
- C18-31 C18 DiDMAPA DiSulfobetaine (100% Trans-)
- MIX-31 C18 DiDMAPA DiSulfobetaine (80:20 Trans-/Cis-)
- C18-32 C18 DiDMAPA DiBetaine (100% Trans-)
- MIX-32 C18 DiDMAPA DiBetaine (80:20 Trans-/Cis-)
- C18-35 C18 DiDMAPA Quat AO (100% Trans-)
- MIX-35 C18 DiDMAPA Quat AO (80:20 Trans-/Cis-)
- C18-36 C18 DiDMAPA Monobetaine (100% Trans-)
- MIX-36 C18 DiDMAPA Monobetaine (80:20 Trans-/Cis-)
- C18-37 C18 DiDMAPA Betaine AO (100% Trans-)
- MIX-37 C18 DiDMAPA Betaine AO (80:20 Trans-/Cis-)
- C18-38 C18 DiDMAPA Betaine Quat (100% Trans-)
- MIX-38 C18 DiDMAPA Betaine Quat (80:20 Trans-/Cis-)
- MIX-42 C18 DiDEA Amide (80:20 Trans-/Cis-)
- MIX-48 C18 Ester DMAPA Betaine (80:20 Trans-/Cis-)
- MIX-70 C18 DMAPA Carboxylate (80:20 Trans-/Cis-)
- TMG-0 Modified Triglyceride Based on Soybean Oil
- the PMTG products have analogous structures to the MTG products.
- the PUTG products have structures as shown below, with the UTG products having structures analogous to the PUTG products.
- This test measures the ability of a cleaning product to remove a greasy dirt soil from a white vinyl tile.
- the test is automated and uses an industry standard Gardner Straight Line Washability Apparatus. A camera and controlled lighting are used to take a live video of the cleaning process. The machine uses a sponge wetted with a known amount of test product. As the machine wipes the sponge across the soiled tile, the video records the result, from which a cleaning percentage can be determined. A total of 10 strokes are made using test formulation diluted 1:32 with water, and cleaning is calculated for each of strokes 1-10 to provide a profile of the cleaning efficiency of the product. The test sample is used as a component of different control formulations depending on whether it anionic, amphoteric, or nonionic.
- a neutral, dilutable all-purpose cleaner is prepared from propylene glycol n-propyl ether (4.0 g), butyl carbitol (4.0 g), sodium citrate (4.0 g), Bio-Soft® EC-690 ethoxylated alcohol (1.0 g, product of Stepan), test sample (0.29 g if 100% active material), and deionized water (to 100.0 g solution).
- the control sample for anionic testing replaces the test sample with Stepanol® WA-Extra PCK (sodium lauryl sulfate, Stepan, 1.0 g, nominally 30% active).
- a neutral, dilutable all-purpose cleaner is prepared from propylene glycol n-propyl ether (4.0 g), butyl carbitol (4.0 g), sodium citrate (4.0 g), Stepanol WA-Extra PCK (sodium lauryl sulfate, 1.0 g), test sample (0.90 g if 100% active material), and deionized water (to 100.0 g solution).
- the control sample for nonionic/amphoteric testing replaces the test sample with Bio-Soft EC690 (ethoxylated alcohol, 1.0 g, nominally 90% active material).
- Soil Composition (from Gardner ASTM D4488-95 Method):
- the particulate medium is composed of (in parts by weight) hyperhumus (39), paraffin oil (1), used motor oil (1.5), Portland cement (17.7), silica 1 (8), molacca black (1.5), iron oxide (0.3), bandy black clay (18), stearic acid (2), and oleic acid (2).
- the oil medium is composed of kerosene (12), Stoddard solvent (12), paraffin oil (1), SAE-10 motor oil (1), Crisco® shortening, product of J.M. Smucker Co. (1), olive oil (3), linoleic acid (3), and squalene (3).
- This test measures the ability of a solvent to clean a greasy dirt soil from a white vinyl tile.
- the soil is the same as used in the Gardner ASTM D4488-95 A5 method, only applied to the tile with a brush.
- the test consists of placing a drop of the test solvent onto the soiled tile, waiting 10 seconds (neat samples), or 30 seconds (diluted), then adding a second drop adjacent to the first, waiting the prescribed time, adding a third drop, etc. After a few minutes the dropping is stopped and the tile rinsed, photographed, and judged for cleaning versus control neat, and in formulation diluted.
- Steposol® M8-10 a mixture of N,N-dimethylcapramide and N,N-dimethylcaprylamide, product of Stepan.
- Diluted samples are made from test actives (5.0 g), Ammonyx® LMDO (lauramidopropylamine oxide, product of Stepan, 10.0 g), and deionized water (q.s. to 100 g).
- the control for the diluted samples replaces the test actives with Steposol M8-10 (5.0 g).
- Results appear in Table 10.
- the C 10 -C 12 amides derived from metathesis of soybean oil outperformed all of the other tested materials as degreaser solvents.
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Abstract
Description
M[X1X2L1L2(L3)n]=Cm═C(R1)R2
where M is a Group 8 transition metal, L1, L2, and L3 are neutral electron donor ligands, n is 0 (such that L3 may not be present) or l, m is 0, 1, or 2, X1 and X2 are anionic ligands, and R1 and R2 are independently selected from H, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups. Any two or more of X1, X2, L1, L2, L3, R1 and R2 can form a cyclic group and any one of those groups can be attached to a support.
TABLE 1 |
Isolation of C10-0 and C12-0 by Distillation |
Distillation | Head temp. | Pot temp. | Vacuum | Weight | C10-0 | C12-0 |
Fractions # | (° C.) | (° C.) | (μtorr) | (g) | (wt %) | (wt %) |
1 | 40-47 | 104-106 | 110 | 6.8 | 80 | 0 |
2 | 45-46 | 106 | 110 | 32.4 | 99 | 0 |
3 | 47-48 | 105-110 | 120 | 223.6 | 99 | 0 |
4 | 49-50 | 110-112 | 120 | 283 | 99 | 0 |
5 | 50 | 106 | 110 | 555 | 99 | 0 |
6 | 50 | 108 | 110 | 264 | 99 | 0 |
7 | 50 | 112 | 110 | 171 | 99 | 0 |
8 | 51 | 114 | 110 | 76 | 97 | 1 |
9 | 65-70 | 126-128 | 110 | 87 | 47 | 23 |
10 | 74 | 130-131 | 110 | 64 | 0 | 75 |
11 | 75 | 133 | 110 | 52.3 | 0 | 74 |
12 | 76 | 135-136 | 110 | 38 | 0 | 79 |
13 | 76 | 136-138 | 100 | 52.4 | 0 | 90 |
14 | 76 | 138-139 | 100 | 25.5 | 0 | 85 |
15 | 76-77 | 140 | 110 | 123 | 0 | 98 |
16 | 78 | 140 | 100 | 426 | 0 | 100 |
TABLE 2A |
General Methods Used to |
Synthesize Compositions |
Composition | Methods | ||
C10-0 | feed | ||
C10-1 | A | ||
C10-6 | B | ||
C10-8 | F | ||
C10-9 | F | ||
C10-10 | F, J | ||
C10-11* | F | ||
C10-14 | H, C, J | ||
C10-17* | E | ||
C10-19* | E, C, J | ||
C10-20 | E, D | ||
C10-21 | E, D, J | ||
C10-22 | E, C | ||
C10-23 | E, C, J | ||
C10-24* | E, C | ||
C10-25* | E | ||
C10-26 | E, J | ||
C10-27 | E | ||
C10-29 | F, J | ||
C10-30 | F, J | ||
C10-32* | K | ||
C10-33* | K | ||
C10-34 | K | ||
C10-35 | K | ||
C10-37 | E, J | ||
C10-38 | E, G | ||
C10-39 | E, G, D | ||
C10-41 | E, G, C | ||
C10-43* | E, G, C | ||
C12-0 | feed | ||
C12-1 | A1 | ||
C12-4 | B | ||
C12-6 | B | ||
C12-8 | F | ||
C12-9 | F | ||
C12-10 | F, J | ||
C12-11 | F | ||
C12-14* | H, C, J | ||
C12-19 | E, C, J | ||
C12-20 | E, D | ||
C12-21 | E, D, J | ||
C12-22 | E, C | ||
C12-23* | E, C, J | ||
C12-24* | E, C | ||
C12-25* | E | ||
C12-26 | E, G | ||
C12-28 | E, G, D | ||
C12-29 | E, J | ||
C12-31 | E | ||
C12-32 | F, J | ||
C12-33 | F, J | ||
C12-34 | K | ||
C12-35 | K | ||
C12-36 | K | ||
C12-37 | K | ||
C12-39 | L | ||
C12-40 | E, G, C | ||
C12-42 | E, J | ||
C12-43 | K | ||
C12-44 | K | ||
C12-46 | E, G, C | ||
C12-47 | F | ||
C12-48 | F | ||
C12-49 | F | ||
C16-0 | feed | ||
C16-1 | A | ||
C16-4 | B | ||
C16-6 | B | ||
C16-8 | F | ||
C16-9 | E | ||
C16-11 | E, J | ||
C16-12 | E, D, J | ||
C16-13 | E, C | ||
C16-15 | E, G | ||
C16-16 | E, G, C | ||
Methods: | |||
A: UFAME sulfonation; | |||
B: alkanolamine transesterification; | |||
C: quaternization to methyl quat, betaine, or sulfobetaine; | |||
D: oxidation of amine to amine oxide; | |||
E: amide from unsaturated ester and primary or secondary amine; | |||
F: ethoxylated fatty acid methyl ester from unsaturated fatty acid; | |||
G: amine from amide by reduction; | |||
H: imidazoline preparation from unsaturated ester + DETA; | |||
J: sulfitation of olefins; | |||
K: estolide preparation; | |||
L: ester hydrolysis to the fatty acid or salt. | |||
*A detailed procedure for synthesizing this composition is included hereinbelow. |
TABLE 2B |
General Methods Used to |
Synthesize Compositions |
Composition | Methods | ||
C18-1 | A | ||
Mix-2 | B | ||
Mix-3 | B | ||
Mix-5 | B | ||
C18-9 | B | ||
Mix-9 | B | ||
Mix-11 | B | ||
Mix-13 | B | ||
Mix-15 | B | ||
Mix-17 | F | ||
Mix-18 | F | ||
Mix-20 | F | ||
Mix-23 | H, C, J | ||
C18-28 | E, C, J | ||
C18-29 | E, D | ||
Mix-29 | E, D | ||
C18-30 | E, D, J | ||
C18-31 | E, C | ||
Mix-31 | E, C | ||
C18-32 | E, C | ||
Mix-32 | E, C | ||
C18-33 | E, C, J | ||
C18-35 | E, C, D | ||
Mix-35 | E, C, D | ||
C18-36 | E, C | ||
Mix-36 | E, C | ||
C18-37 | E, C, D | ||
Mix-37 | E, C, D | ||
C18-38 | E, C | ||
Mix-38 | E, C | ||
Mix-42 | E | ||
Mix-46 | E, D | ||
Mix-48 | E, C | ||
Mix-59 | E | ||
Mix-61 | F, J | ||
C18-63 | K | ||
C18-64 | K | ||
C18-68 | E, J | ||
Mix-70 | E | ||
Mix-73 | E, D | ||
Mix-78 | E | ||
PMTG-6 | E, C | ||
PMTG-11 | E, C | ||
PMTG-12 | E, D | ||
PUTG-6 | E, C | ||
PUTG-11 | E, C | ||
PUTG-12 | E, D | ||
MTG-6 | E, C | ||
MTG-11 | E, C | ||
MTG-12 | E, D | ||
UTG-6 | E, C | ||
UTG-7 | B, C | ||
UTG-9 | B | ||
UTG-11 | E, C | ||
UTG-12 | E, D | ||
UTG-15 | E | ||
UTG-16 | E | ||
Methods: | |||
A: UFAME sulfonation; | |||
B: alkanolamine transesterification; | |||
C: quaternization to methyl quat, betaine, or sulfobetaine; | |||
D: oxidation of amine to amine oxide; | |||
E: amide from unsaturated ester and primary or secondary amine; | |||
F: ethoxylated fatty acid methyl ester from unsaturated fatty acid; | |||
G: amine from amide by reduction; | |||
H: imidazoline preparation from unsaturated ester + DETA; | |||
J: sulfitation of olefins; | |||
K: estolide preparation; | |||
L: ester hydrolysis to the fatty acid or salt. |
TABLE 3 |
Self-Metathesis of Methyl 9-Dodecanoate |
Catalyst Loading | Reaction | C18-0 | |||
Sample | (ppm mol/mol)* | Time (h) | (GC Area %) | ||
A | 100 | 3 | 83.5 | ||
B | 50 | 3 | 82.5 | ||
C | 25 | 3 | 83.0 | ||
D | 10 | 3 | 66.2 | ||
E | 15 | 4 | 90.0 | ||
F | 13 | 4 | 89.9 | ||
G | 10 | 4 | 81.1 | ||
H | 5 | 4 | 50.9 | ||
*ppm mol catalyst/mol methyl 9-dodecenoate |
The tested compounds based on C18 feedstock have the following structures:
C18-1: C18 Sulfonate
C18-31: C18 DiDMAPA DiSulfobetaine (100% Trans-)
MIX-31: C18 DiDMAPA DiSulfobetaine (80:20 Trans-/Cis-)
TABLE 4 |
Summary of Modified Triglyceride Products |
Soybean Oil | Palm Oil |
Self-met. | X-met. | Self-met. | X-met. | ||
MTG-0 | UTG-0 | PMTG-0 | PUTG-0 | ||
DMAPA Betaine Mix | MTG-6 | UTG-6 | PMTG-6 | PUTG-6 |
DMAPA Sulfobetaine | MTG-11 | UTG-11 | PMTG-11 | PUTG-11 |
DMAPA AO | MTG-12 | UTG-12 | PMTG-12 | PUTG-12 |
UTG MDEA ester (2:1) | UTG-9 | |||
UTG DMA amide | UTG-15 | |||
UTG DEA amide | UTG-16 | |||
UTG TEA ester quat | UTG-7 | |||
Hard-Surface Cleaners: Aqueous Degreasers
TABLE 5 |
Control Runs for Gardner Straight Line Washability Test |
Ave. % clean after 2, 4, 6, 8, or 10 swipes |
2 | 4 | 6 | 8 | 10 | ||
Control 1 | 52.4 | 59.0 | 62.5 | 62.8 | 63.9 | ||
Control 2 | 47.0 | 57.3 | 61.0 | 63.7 | 65.2 | ||
Control 3 | 54.6 | 61.4 | 64.3 | 68.4 | 72.2 | ||
Control 4 | 52.5 | 58.2 | 59.5 | 60.9 | 63.3 | ||
Control 5 | 50.8 | 59.2 | 63.9 | 65.3 | 67.1 | ||
Control 6 | 51.2 | 57.6 | 62.7 | 62.6 | 66.0 | ||
Control 7 | 52.3 | 56.0 | 61.5 | 64.3 | 65.0 | ||
Control 8 | 49.6 | 55.9 | 56.8 | 62.8 | 64.1 | ||
Control 9 | 55.5 | 61.5 | 66.0 | 65.9 | 68.4 | ||
Control 10 | 60.3 | 63.5 | 66.2 | 65.8 | 68.7 | ||
Control 11 | 53.0 | 61.0 | 63.6 | 64.6 | 66.2 | ||
Control 12 | 65.6 | 71.4 | 75.0 | 75.3 | 72.6 | ||
Control 13 | 67.6 | 72.6 | 76.0 | 76.3 | 76.5 | ||
Control 14 | 61.2 | 65.5 | 67.7 | 69.1 | 69.7 | ||
Control 15 | 59.7 | 63.6 | 64.5 | 69.5 | 69.5 | ||
Control 16 | 50.9 | 61.5 | 63.1 | 64.0 | 67.7 | ||
Control 17 | 54.7 | 63.7 | 64.6 | 66.1 | 69.6 | ||
Control 18 | 62.2 | 67.6 | 70.4 | 71.7 | 71.7 | ||
Control 19 | 60.8 | 68.0 | 70.6 | 71.4 | 71.5 | ||
Control 20 | 65.0 | 70.7 | 72.2 | 73.7 | 74.0 | ||
Control 21 | 64.6 | 68.8 | 70.5 | 71.2 | 72.0 | ||
Control 22 | 51.3 | 57.7 | 61.5 | 64.1 | 68.0 | ||
Control 23 | 60.2 | 64.7 | 66.7 | 68.3 | 68.7 | ||
Control 24 | 52.8 | 61.6 | 63.3 | 64.9 | 65.7 | ||
TABLE 6 |
Nonionic/Amphoteric Test Samples: Inventive Examples |
Con. | Ave. % clean |
Sample | # | Compound class | 2 | 4 | 6 | 8 | 10 | Rating |
C10-11 | 1 | high-EO ethoxylate | 57.7 | 64.8 | 70.2 | 70.5 | 71.9 | superior |
C10-19 | 2 | DMAPA quat sulfonate | 55.2 | 62.0 | 65.5 | 66.9 | 67.8 | superior |
C12-14 | 1 | DETA quat sulfonate | 58.0 | 65.7 | 68.5 | 69.0 | 69.4 | superior |
C12-24 | 3 | DMAPA sulfobetaine | 64.2 | 70.6 | 72.3 | 76.6 | 80.2 | superior |
UTG-11 | 4 | DMAPA sulfobetaine | 63.3 | 65.3 | 69.1 | 69.9 | 70.5 | superior |
C10-9 | 5 | mid-EO ethoxylate | 52.2 | 55.1 | 60.9 | 64.7 | 64.3 | equal |
C10-14 | 6 | DETA quat sulfonate | 59.0 | 65.2 | 65.6 | 67.7 | 67.4 | equal |
C10-27 | 7 | DEA amide | 53.9 | 56.0 | 58.4 | 62.0 | 65.2 | equal |
C10-39 | 6 | amine oxide | 47.4 | 56.8 | 60.4 | 59.8 | 61.9 | equal |
C10-41 | 6 | betaine | 56.2 | 63.0 | 63.1 | 63.7 | 64.2 | equal |
C10-43 | 23 | sulfobetaine | 55.5 | 63.2 | 66.0 | 66.5 | 67.2 | equal |
C12-9 | 8 | mid-EO ethoxylate | 48.8 | 54.8 | 59.4 | 59.8 | 61.4 | equal |
C12-11 | 9 | high-EO ethoxylate | 62.5 | 67.2 | 70.7 | 70.1 | 69.6 | equal |
C12-19 | 9 | DMAPA quat sulfonate | 55.5 | 61.7 | 64.5 | 66.1 | 66.6 | equal |
C12-31 | 5 | DEA amide | 57.3 | 64.2 | 67.1 | 69.0 | 69.6 | equal |
C12-46 | 23 | sulfobetaine | 56.6 | 61.2 | 63.5 | 64.6 | 65.3 | equal |
C12-49 | 4 | mid-EO ethoxylate | 53.1 | 57.3 | 59.3 | 59.4 | 61.2 | equal |
C16-9 | 11 | DMAPA amide | 48.0 | 53.9 | 60.1 | 62.2 | 64.7 | equal |
C16-13 | 19 | DMAPA betaine | 50.7 | 62.5 | 63.4 | 65.3 | 66.2 | equal |
Mix-3 | 19 | TEA ester | 55.0 | 61.6 | 63.3 | 65.6 | 66.7 | equal |
Mix-5 | 4 | TEA ester | 60.1 | 62.0 | 64.7 | 66.3 | 67.1 | equal |
Mix-15 | 18 | DMEA ester | 47.0 | 60.9 | 62.8 | 64.3 | 65.5 | equal |
Mix-18 | 18 | mid-EO ethoxylate | 57.8 | 61.8 | 62.3 | 63.4 | 66.2 | equal |
Mix-20 | 18 | high-EOB ethoxylate | 59.4 | 63.2 | 67.3 | 67.4 | 69.2 | equal |
Mix-23 | 20 | diDETA diquat sulfonate | 58.9 | 68.2 | 69.0 | 71.0 | 71.2 | equal |
Mix-32 | 11 | diDMAPA dibetaine | 49.6 | 58.1 | 59.4 | 62.1 | 65.5 | equal |
C18-36 | 8 | diDMAPA monobetaine | 50.2 | 57.3 | 59.9 | 65.5 | 67.8 | equal |
Mix-36 | 11 | diDMAPA monobetaine | 40.1 | 53.7 | 58.4 | 60.4 | 63.6 | equal |
C18-37 | 8 | diDMAPA betaine/AO | 54.2 | 60.1 | 62.4 | 63.9 | 66.6 | equal |
Mix-37 | 4 | diDMAPA betaine/AO | 57.4 | 61.6 | 62.9 | 64.6 | 65.5 | equal |
Mix-38 | 18 | diDMAPA betaine quat | 44.5 | 57.1 | 62.4 | 66.0 | 67.8 | equal |
Mix-42 | 18 | diDEA amide | 65.6 | 66.6 | 70.8 | 71.5 | 73.3 | equal |
Mix-48 | 21 | DMAPA betaine ester | 55.3 | 62.6 | 63.9 | 65.7 | 65.9 | equal |
Mix-73 | 21 | DMAPA AO carboxylate | 55.6 | 60.6 | 61.8 | 62.9 | 64.2 | equal |
PUTG-11 | 7 | DMAPA sulfobetaine | 53.9 | 60.5 | 62.2 | 66.4 | 67.1 | equal |
MTG-6 | 10 | DMAPA betaine | 62.8 | 66.7 | 68.7 | 70.2 | 72.7 | equal |
MTG-11 | 7 | DMAPA sulfobetaine | 49.9 | 54.5 | 54.7 | 58.8 | 61.2 | equal |
UTG-6 | 11 | DMAPA betaine | 51.9 | 60.1 | 61.9 | 62.8 | 63.3 | equal |
UTG-7 | 4 | TEA ester quat | 59.5 | 62.7 | 63.7 | 66.0 | 66.4 | equal |
UTG-12 | 4 | DMAPA amine oxide | 43.3 | 51.2 | 54.3 | 55.0 | 57.4 | equal |
TABLE 7 |
Nonionic/Amphoteric Test Samples: Comparative Examples |
Con. | Ave. % clean |
Sample | # | Compound class | 2 | 4 | 6 | 8 | 10 | Rating |
C10-20 | 10 | DMAPA amine oxide | 59.0 | 61.7 | 62.2 | 61.8 | 63.9 | inferior |
C10-22 | 12 | DMAPA betaine | 57.3 | 63.9 | 66.6 | 68.8 | 72.2 | inferior |
C10-24 | 13 | DMAPA sulfobetaine | 53.7 | 56.0 | 63.2 | 65.3 | 64.4 | inferior |
C12-20 | 3 | DMAPA amine oxide | 30.2 | 35.9 | 39.1 | 42.7 | 46.1 | inferior |
C12-22 | 13 | DMAPA betaine | 47.5 | 55.2 | 58.1 | 61.6 | 66.4 | inferior |
C12-28 | 14 | amine oxide | 27.7 | 38.6 | 42.7 | 46.7 | 47.9 | inferior |
C12-40 | 14 | betaine | 36.9 | 43.8 | 49.9 | 50.6 | 52.9 | inferior |
C12-47 | 4 | mid-EO ethoxylate | 40.5 | 44.7 | 45.2 | 46.0 | 46.2 | inferior |
C12-48 | 4 | mid-EO ethoxylate | 38.7 | 47.0 | 48.1 | 48.1 | 48.3 | inferior |
C16-8 | 11 | mid-EO ethoxylate | 34.9 | 40.3 | 42.0 | 42.8 | 43.3 | inferior |
C16-16 | 20 | betaine | 58.1 | 60.4 | 62.2 | 62.9 | 63.4 | inferior |
C18-29 | 15 | diDMAPA amine oxide | 38.5 | 42.8 | 49.9 | 51.0 | 51.4 | inferior |
Mix-29 | 22 | diDMAPA amine oxide | 41.6 | 49.7 | 51.6 | 53.5 | 56.6 | inferior |
C18-31 | 15 | diDMAPA disulfobetaine | 45.2 | 50.1 | 52.3 | 53.3 | 53.3 | inferior |
Mix-31 | 22 | diDMAPA disulfobetaine | 45.6 | 53.8 | 57.5 | 59.2 | 59.6 | inferior |
C18-32 | 15 | diDMAPA dibetaine | 48.9 | 56.9 | 58.9 | 60.3 | 61.9 | inferior |
C18-35 | 15 | diDMAPA quat AO | 39.0 | 48.4 | 52.4 | 55.2 | 57.4 | inferior |
Mix-35 | 11 | diDMAPA quat AO | 36.0 | 43.0 | 49.2 | 52.0 | 56.2 | inferior |
C18-38 | 17 | diDMAPA quat betaine | 34.4 | 46.4 | 52.5 | 57.7 | 59.4 | inferior |
Mix-46 | 21 | ester DMAPA AO | 38.0 | 49.9 | 53.0 | 54.2 | 57.0 | inferior |
Mix-70 | 21 | DMAPA carboxylate | 42.2 | 53.4 | 55.8 | 56.2 | 57.6 | inferior |
Mix-78 | 20 | DMA amide carboxylate | 58.4 | 60.4 | 60.7 | 62.0 | 61.6 | inferior |
PMTG-6 | 3 | DMAPA betaine | 51.7 | 55.8 | 56.6 | 57.6 | 60.0 | inferior |
PMTG-11 | 3 | DMAPA sulfobetaine | 49.0 | 52.1 | 55.4 | 61.7 | 62.1 | inferior |
PMTG-12 | 3 | DMAPA amine oxide | 34.8 | 40.3 | 44.4 | 48.0 | 49.8 | inferior |
PUTG-6 | 3 | DMAPA betaine | 44.4 | 50.5 | 52.9 | 55.9 | 57.0 | inferior |
PUTG-12 | 7 | DMAPA amine oxide | 42.7 | 46.4 | 48.0 | 53.0 | 56.0 | inferior |
MTG-12 | 7 | DMAPA amine oxide | 42.7 | 47.6 | 51.9 | 54.5 | 56.1 | inferior |
TABLE 8 |
Anionic Test Samples: Inventive Examples |
Con. | Ave. % clean |
Sample | # | Compound class | 2 | 4 | 6 | 8 | 10 | Rating |
C10-33 | 1 | sulfo-estolide | 52.6 | 58.8 | 67.6 | 69.2 | 69.9 | superior |
C12-23 | 2 | DMAPA betaine sulfonate | 55.7 | 61.5 | 64.8 | 67.4 | 70.1 | superior |
C10-1 | 10 | sulfonate | 61.8 | 65.6 | 68.0 | 68.7 | 70.5 | equal |
C10-10 | 16 | mid-EO ethox sulfonate | 49.9 | 57.5 | 59.7 | 61.0 | 62.6 | equal |
C10-21 | 3 | DMAPA AO sulfonate | 51.1 | 56.4 | 57.4 | 63.3 | 65.9 | equal |
C10-26 | 3 | DMA amide sulfonate | 53.2 | 57.0 | 61.7 | 65.4 | 66.9 | equal |
C10-29 | 16 | low-EO ethox sulfonate | 54.4 | 61.6 | 63.1 | 65.6 | 67.9 | equal |
C10-30 | 6 | high-EO ethox sulfonate | 58.8 | 63.6 | 68.3 | 68.8 | 70.6 | equal |
C10-34 | 3 | sulfo-estolide | 50.9 | 54.0 | 58.5 | 60.5 | 64.6 | equal |
C10-35 | 5 | sulfo-estolide | 56.0 | 63.1 | 66.5 | 68.0 | 71.0 | equal |
C10-37 | 16 | DMA amide sulfonate | 56.1 | 59.6 | 66.0 | 67.9 | 69.1 | equal |
C12-1 | 16 | sulfonate | 52.6 | 60.9 | 62.6 | 65.5 | 68.0 | equal |
C12-10 | 6 | mid-EO ethox sulfonate | 57.1 | 61.2 | 66.6 | 66.0 | 66.8 | equal |
C12-21 | 11 | DMAPA AO sulfonate | 58.2 | 63.9 | 63.7 | 64.2 | 65.3 | equal |
C12-34 | 8 | sulfo-estolide | 52.2 | 59.4 | 61.3 | 63.8 | 65.3 | equal |
C12-35 | 9 | sulfo-estolide | 57.1 | 64.8 | 68.2 | 70.5 | 72.5 | equal |
C12-36 | 9 | sulfo-estolide | 58.2 | 62.0 | 68.0 | 70.9 | 72.2 | equal |
C12-37 | 9 | sulfo-estolide | 56.3 | 65.8 | 68.3 | 71.1 | 72.3 | equal |
C12-42 | 11 | DMAPA sulfonate | 54.5 | 60.2 | 61.5 | 63.5 | 65.3 | equal |
C12-43 | 24 | sulfo-estolide | 57.8 | 62.6 | 64.3 | 64.9 | 66.2 | equal |
C12-44 | 24 | sulfo-estolide | 58.6 | 62.9 | 64.4 | 65.6 | 67.0 | equal |
C16-1 | 20 | sulfonate | 62.7 | 69.2 | 69.4 | 70.2 | 70.2 | equal |
C16-12 | 20 | DMAPA AO sulfonate | 65.7 | 69.7 | 70.3 | 71.0 | 71.0 | equal |
C18-1 | 15 | sulfonate | 52.7 | 59.2 | 59.6 | 62.1 | 64.0 | equal |
C18-28 | 17 | DMAPA diquat sulfonate | 52.2 | 61.1 | 64.3 | 67.6 | 69.2 | equal |
C18-30 | 17 | diDMAPA AO sulfonate | 55.3 | 59.2 | 64.1 | 65.9 | 66.2 | equal |
C18-33 | 17 | DMAPA dibetaine sulfonate | 58.7 | 63.3 | 66.2 | 67.6 | 68.1 | equal |
Mix-61 | 21 | low-EO ethox sulfonate | 58.8 | 62.5 | 64.8 | 65.0 | 65.5 | equal |
C18-63 | 17 | sulfo-estolide | 52.4 | 55.3 | 64.2 | 66.0 | 66.9 | equal |
C18-64 | 17 | sulfo-estolide | 52.2 | 62.0 | 64.6 | 65.6 | 67.0 | equal |
C18-68 | 17 | diDMAPA sulfonate | 53.9 | 63.3 | 66.8 | 67.6 | 70.0 | equal |
TABLE 9 |
Anionic Test Samples: Comparative Examples |
Con. | Ave. % clean |
Sample | # | Compound class | 2 | 4 | 6 | 8 | 10 | Rating |
C10-23 | 13 | DMAPA betaine sulfonate | 56.1 | 59.7 | 61.3 | 64.8 | 68.0 | inferior |
C10-32 | 13 | sulfo-estolide | 54.2 | 60.4 | 63.5 | 67.0 | 67.2 | inferior |
C12-29 | 14 | DMA amide sulfonate | 50.0 | 53.4 | 56.2 | 58.5 | 59.4 | inferior |
C12-32 | 14 | high-EO ethox sulfonate | 42.3 | 49.9 | 51.5 | 53.2 | 53.5 | inferior |
C12-33 | 14 | low-EO ethox sulfonate | 46.9 | 55.3 | 57.1 | 58.4 | 59.5 | inferior |
C16-11 | 11 | DMAPA sulfonate | 28.8 | 32.7 | 34.9 | 37.1 | 37.2 | inferior |
TABLE 10 |
Performance as a Solvent in Industrial Degreasers |
Sample | Composition class | Neat | Diluted | ||
Inventive Examples |
C10-25 | DMA amide | superior | superior | |
C12-25 | DMA amide | equal | superior |
Comparative Examples |
C10-0 | unsaturated methyl ester | inferior | inferior | ||
C10-6 | DMEA ester | inferior | inferior | ||
C10-8 | low-EO ethoxylate | inferior | inferior | ||
C10-17 | DMAPA amide | inferior | inferior | ||
C10-38 | amine | inferior | inferior | ||
C12-0 | unsaturated methyl ester | inferior | inferior | ||
C12-4 | MDEA ester | inferior | inferior | ||
C12-6 | DMEA ester | inferior | inferior | ||
C12-8 | low-EO ethoxylate | inferior | inferior | ||
C12-17 | DMAPA amide | inferior | inferior | ||
C12-26 | amine | inferior | inferior | ||
C12-39 | fatty acid | inferior | inferior | ||
C16-0 | unsaturated methyl ester | inferior | inferior | ||
C16-4 | TEA ester | inferior | inferior | ||
C16-6 | MDEA ester | inferior | inferior | ||
C16-14 | DMA amide | inferior | inferior | ||
C16-15 | amine | inferior | inferior | ||
Mix-2 | IPA ester | inferior | inferior | ||
C18-9 | MDEA ester | inferior | inferior | ||
Mix-9 | MDEA ester | inferior | inferior | ||
Mix-11 | MDEA ester | inferior | inferior | ||
Mix-13 | MDEA ester | inferior | inferior | ||
Mix-17 | low-EO ethoxylate | inferior | inferior | ||
Mix-59 | DMA ester | inferior | inferior | ||
UTG-9 | MDEA ester | inferior | inferior | ||
UTG-15 | DMA amide | inferior | inferior | ||
UTG-16 | DEA amide | inferior | inferior | ||
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